Leeward Islands
Leeward Islands, Trade-Wind Sailing Across the Northern Caribbean
Seen from the sea, the Leeward Islands form a chain rather than a cluster. Stretching across the northeastern Caribbean, they include islands such as Antigua, Saint Martin, and Saint Barthélemy, among others. Unlike compact archipelagos, the Leewards are defined by visible horizons and progressive island crossings.
Each island presents a distinct profile. Some are volcanic with elevated interiors and indented coastlines, others flatter with long beaches and reef-fringed shores. From the water, the sense of movement between separate landmasses defines the sailing rhythm.
The trade winds shape daily navigation. Easterly breezes remain consistent throughout much of the season, encouraging steady passages between islands. Distances are moderate, longer than in sheltered island systems but manageable within structured itineraries.
Why sail the Leeward Islands? Because they combine open-water energy with navigable spacing. Sailing here feels expansive yet sequential.
Colonial Layers and Maritime Identity
The Leeward Islands reflect layered colonial histories. British, French, and Dutch influences remain visible in architecture, language, and administrative systems. Ports developed as strategic naval and trade hubs, shaping coastal infrastructure that persists today.
Maritime culture remains central. Fishing communities, yacht harbors, and regatta traditions coexist within small-scale island environments. Antigua in particular hosts internationally recognized sailing events, reinforcing the region’s strong nautical identity.
What defines the Leeward Islands’ character?
Diversity within continuity. Each island retains a distinct governance and cultural tone, yet all share trade-wind orientation and maritime reliance.
Sailing highlights these differences. Approaching Saint Martin differs visually and culturally from entering Antigua or Saint Barthélemy, yet the ocean rhythm remains constant.
The Leeward Islands are not uniform. They are sequential.
Climate and Sailing Conditions in the Leeward Islands
June is the hottest month in Havana with an average temperature of 27°C (81°F) and the coldest is January at 21°C (70°F) with the most daily sunshine hours at 11 in July. The wettest month is June with an average of 80mm of rain. The best month to swim in the sea is in August when the average sea temperature is 30°C (86°F).
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